Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113005982/bg3155sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005982/bg3155Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005982/bg3155IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113005982/bg3155IIIsup4.hkl |
CCDC references: 934602; 934603; 934604
For all compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Zn(C26H18N3O2)Cl] | F(000) = 1032 |
Mr = 505.25 | Dx = 1.523 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 1024 reflections |
a = 12.925 (3) Å | θ = 2.8–19.2° |
b = 10.175 (2) Å | µ = 1.27 mm−1 |
c = 17.334 (4) Å | T = 298 K |
β = 104.804 (4)° | Block, yellow |
V = 2204.1 (8) Å3 | 0.12 × 0.10 × 0.07 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3927 independent reflections |
Radiation source: fine-focus sealed tube | 1921 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.102 |
φ and ω scans | θmax = 25.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −15→13 |
Tmin = 0.863, Tmax = 0.917 | k = −12→11 |
10985 measured reflections | l = −20→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 0.87 | w = 1/[σ2(Fo2) + (0.0149P)2] where P = (Fo2 + 2Fc2)/3 |
3927 reflections | (Δ/σ)max = 0.001 |
298 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
Experimental. Details for 2-(3-(pyridin-4-yl)phenyl)-1H-benzimidazole: 1H NMR (300 MHz, DMSO-d6, 298 K, TMS, δ, cm-1): 13.05 (s, 1H, –NH), 8.72–8.70 (d, 2H, –C5H4N), 8.59 (s, 1H, –C6H4), 8.29–8.27 (d, 1H, –C6H4), 7.94–7.92 (d, 1H, –C6H4), 7.83–7.82 (d, 2H, –C6H4), 7.73–7.70 (t, 1H, –C6H4), 7.65–7.63 (s, 2H, –C6H4), 7.24–7.23 (m, 2H, –C6H4). IR (KBr pellet, ν, cm-1): 3047 (m), 1600 (s), 1537 (m), 1477 (s), 1432 (s), 1398 (m), 1315 (w), 1275 (m), 1223 (m), 1107 (w), 1069 (w), 1001 (m), 959 (w), 899 (w), 831 (s), 802 (s), 770 (w), 738 (s), 694 (m), 617 (s), 595 (w), 562 (w), 542 (w), 521 (w), 456 (w), 429 (w). Elemental analysis, calculated for C24H17N3: C 82.97, H 4.93, N 12.10%; found: C 82.96, H 4.94, N 12.11%. For 2-[3-(pyridin-4-yl)phenyl]-1-(4-carboxyl benzyl)benzimidazole (HL): 1H NMR (300 MHz, DMSO-d6, 298 K, TMS, δ, cm-1): 8.61 (d, 1H, –C6H4), 7.99–7.97 (d, 2H, –C5H4N), 7.94 (d, 1H, –C6H4), 7.88 (d, 1H, –C6H4), 7.85–7.83 (d, 2H, –C5H4N), 7.70 (s, 1H, –C6H4), 7.64–7.62 (d, 2H, –C6H4), 7.54–7.53 (m, 1H, –C6H4), 7.30–7.29 (d, 2H, –C6H4), 7.16–7.13 (m, 2H, –C6H4), 5.72 (s, 2H, –CH2). IR (KBr pellet, ν, cm-1): 3452 (s), 1610 (s), 1511 (w), 1479 (w), 1455 (m), 1384 (m), 1328 (s), 1290 (m), 1114 (m), 1069 (m), 1018 (w), 904 (w), 831 (w), 797 (s), 751 (s), 696 (m), 623 (w), 515 (w). Elemental analysis, calculated for C26H19N3O2: C 77.02, H 4.72, N 10.36%; found: C77.00, H 4.73, N 10.34%. Details for (I): IR (KBr pellet, ν, cm-1): 3422 (m), 1620 (s), 1566 (m), 1466 (w), 1420 (s), 1362 (s), 1235 (s), 1174 (m), 1071 (w), 1025 (w), 900 (w), 834 (s), 799 (s), 771 (s), 759 (s), 686 (w), 627 (w), 575 (w), 430 (w). Details for (II): IR (KBr pellet, ν, cm-1): 3454 (m), 1620 (s), 1567 (m), 1467 (m), 1419 (s), 1363 (s), 1234 (w), 1072 (w), 1025 (w), 920 (w), 901 (w), 834 (m), 800 (s), 772 (s), 759 (s), 686 (s), 627 (w), 576 (w), 466 (w), 431 (w). Details for (III): IR (KBr pellet, ν, cm-1): 3420 (m), 1621 (s), 1567 (w), 1512 (w), 1468 (m), 1456 (m), 1419 (m), 1371 (s), 1295 (w), 1233 (w), 1073 (w), 1026 (w), 902 (w), 834 (m), 800 (s), 772 (s), 760 (s), 686 (w), 627 (w), 466 (w), 433 (w). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9081 (5) | 1.2272 (7) | 0.6088 (4) | 0.0423 (16) | |
C2 | 0.8763 (4) | 1.1306 (6) | 0.5392 (3) | 0.0366 (15) | |
C3 | 0.8283 (4) | 1.1749 (6) | 0.4634 (3) | 0.0494 (17) | |
H3 | 0.8141 | 1.2640 | 0.4547 | 0.059* | |
C4 | 0.8010 (4) | 1.0872 (6) | 0.3999 (3) | 0.0459 (16) | |
H4 | 0.7699 | 1.1188 | 0.3489 | 0.055* | |
C5 | 0.8189 (4) | 0.9556 (6) | 0.4110 (3) | 0.0355 (14) | |
C6 | 0.8677 (4) | 0.9114 (5) | 0.4872 (3) | 0.0438 (16) | |
H6 | 0.8815 | 0.8222 | 0.4961 | 0.053* | |
C7 | 0.8962 (4) | 0.9988 (6) | 0.5500 (3) | 0.0419 (17) | |
H7 | 0.9295 | 0.9675 | 0.6007 | 0.050* | |
C8 | 0.7875 (4) | 0.8557 (5) | 0.3441 (3) | 0.0427 (16) | |
H8A | 0.8505 | 0.8323 | 0.3264 | 0.051* | |
H8B | 0.7620 | 0.7768 | 0.3647 | 0.051* | |
C9 | 0.5975 (5) | 0.9003 (5) | 0.2669 (3) | 0.0359 (15) | |
C10 | 0.5454 (4) | 0.8345 (5) | 0.3229 (3) | 0.0358 (15) | |
C11 | 0.4693 (5) | 0.7409 (6) | 0.2926 (3) | 0.0499 (17) | |
H11 | 0.4522 | 0.7212 | 0.2384 | 0.060* | |
C12 | 0.4180 (5) | 0.6759 (6) | 0.3424 (3) | 0.064 (2) | |
H12 | 0.3658 | 0.6135 | 0.3215 | 0.077* | |
C13 | 0.4441 (5) | 0.7037 (6) | 0.4229 (3) | 0.0574 (19) | |
H13 | 0.4098 | 0.6588 | 0.4561 | 0.069* | |
C14 | 0.5208 (4) | 0.7977 (6) | 0.4553 (3) | 0.0381 (15) | |
C15 | 0.5710 (4) | 0.8612 (5) | 0.4038 (3) | 0.0378 (15) | |
H15 | 0.6233 | 0.9236 | 0.4244 | 0.045* | |
C16 | 0.5467 (5) | 0.8312 (6) | 0.5420 (3) | 0.0381 (15) | |
C17 | 0.4860 (4) | 0.7870 (6) | 0.5910 (3) | 0.0534 (18) | |
H17 | 0.4268 | 0.7339 | 0.5702 | 0.064* | |
C18 | 0.5119 (5) | 0.8207 (6) | 0.6712 (3) | 0.0565 (19) | |
H18 | 0.4700 | 0.7873 | 0.7030 | 0.068* | |
C19 | 0.6520 (4) | 0.9430 (6) | 0.6580 (3) | 0.0483 (17) | |
H19 | 0.7094 | 0.9981 | 0.6798 | 0.058* | |
C20 | 0.6313 (4) | 0.9113 (6) | 0.5775 (3) | 0.0484 (17) | |
H20 | 0.6752 | 0.9447 | 0.5472 | 0.058* | |
C21 | 0.7232 (4) | 0.9565 (5) | 0.2073 (3) | 0.0347 (14) | |
C22 | 0.6227 (4) | 0.9891 (5) | 0.1599 (3) | 0.0351 (15) | |
C23 | 0.6126 (5) | 1.0406 (5) | 0.0842 (3) | 0.0422 (15) | |
H23 | 0.5463 | 1.0653 | 0.0521 | 0.051* | |
C24 | 0.7038 (6) | 1.0536 (5) | 0.0585 (3) | 0.0530 (18) | |
H24 | 0.6985 | 1.0847 | 0.0072 | 0.064* | |
C25 | 0.8040 (5) | 1.0220 (5) | 0.1068 (4) | 0.0513 (17) | |
H25 | 0.8641 | 1.0336 | 0.0873 | 0.062* | |
C26 | 0.8165 (4) | 0.9734 (5) | 0.1835 (3) | 0.0468 (15) | |
H26 | 0.8834 | 0.9534 | 0.2167 | 0.056* | |
Cl1 | 0.26106 (12) | 0.88894 (16) | 0.15025 (9) | 0.0672 (5) | |
N1 | 0.5935 (4) | 0.8981 (5) | 0.7049 (2) | 0.0448 (13) | |
N2 | 0.5446 (3) | 0.9555 (4) | 0.1986 (2) | 0.0378 (12) | |
N3 | 0.7053 (4) | 0.9028 (4) | 0.2762 (2) | 0.0340 (12) | |
O1 | 0.8687 (3) | 1.3399 (4) | 0.5960 (2) | 0.0569 (12) | |
O2 | 0.9702 (3) | 1.1885 (4) | 0.6704 (2) | 0.0730 (14) | |
Zn1 | 0.39335 (5) | 1.03294 (7) | 0.18148 (4) | 0.0451 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.031 (4) | 0.056 (5) | 0.040 (4) | −0.005 (3) | 0.009 (3) | −0.012 (4) |
C2 | 0.033 (4) | 0.043 (5) | 0.035 (4) | 0.002 (3) | 0.011 (3) | −0.003 (3) |
C3 | 0.054 (5) | 0.045 (5) | 0.047 (4) | 0.001 (3) | 0.009 (4) | −0.003 (3) |
C4 | 0.059 (4) | 0.044 (5) | 0.029 (3) | 0.000 (3) | 0.000 (3) | 0.002 (3) |
C5 | 0.038 (4) | 0.033 (4) | 0.033 (3) | 0.002 (3) | 0.004 (3) | −0.001 (3) |
C6 | 0.040 (4) | 0.042 (4) | 0.049 (4) | 0.012 (3) | 0.011 (3) | 0.000 (3) |
C7 | 0.035 (4) | 0.061 (6) | 0.027 (3) | 0.007 (3) | 0.003 (3) | 0.003 (3) |
C8 | 0.042 (4) | 0.042 (4) | 0.038 (3) | 0.004 (3) | −0.001 (3) | −0.002 (3) |
C9 | 0.041 (4) | 0.034 (4) | 0.034 (4) | 0.002 (3) | 0.011 (3) | 0.002 (3) |
C10 | 0.037 (4) | 0.038 (4) | 0.031 (3) | 0.002 (3) | 0.006 (3) | 0.008 (3) |
C11 | 0.062 (5) | 0.060 (5) | 0.026 (3) | −0.010 (4) | 0.009 (3) | 0.004 (3) |
C12 | 0.061 (5) | 0.078 (6) | 0.051 (4) | −0.030 (4) | 0.009 (4) | −0.008 (4) |
C13 | 0.066 (5) | 0.068 (6) | 0.040 (4) | −0.017 (4) | 0.015 (4) | 0.003 (3) |
C14 | 0.040 (4) | 0.043 (5) | 0.033 (3) | 0.002 (3) | 0.012 (3) | 0.008 (3) |
C15 | 0.034 (4) | 0.042 (4) | 0.035 (3) | 0.002 (3) | 0.004 (3) | 0.004 (3) |
C16 | 0.045 (4) | 0.038 (4) | 0.032 (3) | 0.005 (3) | 0.012 (3) | 0.006 (3) |
C17 | 0.060 (5) | 0.059 (5) | 0.041 (4) | −0.020 (3) | 0.012 (4) | 0.006 (3) |
C18 | 0.072 (6) | 0.069 (6) | 0.032 (4) | −0.006 (4) | 0.019 (4) | 0.003 (3) |
C19 | 0.037 (4) | 0.064 (5) | 0.043 (4) | −0.002 (3) | 0.009 (3) | 0.007 (3) |
C20 | 0.045 (4) | 0.068 (5) | 0.036 (4) | −0.004 (3) | 0.019 (3) | 0.006 (3) |
C21 | 0.042 (4) | 0.033 (4) | 0.030 (3) | −0.003 (3) | 0.012 (3) | −0.002 (3) |
C22 | 0.047 (4) | 0.031 (4) | 0.027 (3) | −0.012 (3) | 0.008 (3) | −0.006 (3) |
C23 | 0.055 (4) | 0.039 (4) | 0.030 (3) | −0.003 (3) | 0.008 (3) | −0.004 (3) |
C24 | 0.091 (6) | 0.040 (4) | 0.034 (4) | −0.008 (4) | 0.026 (4) | −0.009 (3) |
C25 | 0.065 (5) | 0.042 (4) | 0.058 (4) | −0.007 (4) | 0.037 (4) | −0.007 (4) |
C26 | 0.045 (4) | 0.045 (4) | 0.054 (4) | −0.005 (3) | 0.020 (3) | −0.011 (3) |
Cl1 | 0.0565 (12) | 0.0732 (14) | 0.0678 (11) | −0.0180 (9) | 0.0083 (9) | 0.0008 (9) |
N1 | 0.056 (4) | 0.047 (4) | 0.032 (3) | 0.001 (3) | 0.012 (3) | 0.000 (2) |
N2 | 0.037 (3) | 0.051 (3) | 0.024 (2) | −0.002 (3) | 0.005 (2) | 0.004 (2) |
N3 | 0.031 (3) | 0.040 (3) | 0.028 (3) | −0.001 (2) | 0.001 (3) | −0.003 (2) |
O1 | 0.078 (3) | 0.044 (3) | 0.044 (3) | 0.001 (3) | 0.008 (2) | −0.016 (2) |
O2 | 0.068 (3) | 0.090 (4) | 0.047 (3) | 0.022 (3) | −0.012 (3) | −0.018 (3) |
Zn1 | 0.0471 (5) | 0.0515 (5) | 0.0347 (4) | 0.0005 (4) | 0.0068 (3) | 0.0055 (4) |
C1—O2 | 1.226 (6) | C14—C16 | 1.494 (6) |
C1—O1 | 1.250 (6) | C15—H15 | 0.9300 |
C1—C2 | 1.529 (7) | C16—C17 | 1.370 (6) |
C2—C7 | 1.370 (7) | C16—C20 | 1.377 (7) |
C2—C3 | 1.377 (7) | C17—C18 | 1.389 (6) |
C3—C4 | 1.391 (7) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—N1 | 1.326 (6) |
C4—C5 | 1.364 (7) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—N1 | 1.324 (6) |
C5—C6 | 1.386 (6) | C19—C20 | 1.389 (6) |
C5—C8 | 1.516 (6) | C19—H19 | 0.9300 |
C6—C7 | 1.381 (6) | C20—H20 | 0.9300 |
C6—H6 | 0.9300 | C21—C26 | 1.381 (6) |
C7—H7 | 0.9300 | C21—N3 | 1.385 (6) |
C8—N3 | 1.451 (6) | C21—C22 | 1.388 (6) |
C8—H8A | 0.9700 | C22—C23 | 1.387 (6) |
C8—H8B | 0.9700 | C22—N2 | 1.391 (6) |
C9—N2 | 1.331 (6) | C23—C24 | 1.369 (7) |
C9—N3 | 1.362 (6) | C23—H23 | 0.9300 |
C9—C10 | 1.475 (6) | C24—C25 | 1.388 (7) |
C10—C11 | 1.373 (6) | C24—H24 | 0.9300 |
C10—C15 | 1.384 (6) | C25—C26 | 1.390 (6) |
C11—C12 | 1.384 (7) | C25—H25 | 0.9300 |
C11—H11 | 0.9300 | C26—H26 | 0.9300 |
C12—C13 | 1.379 (7) | Zn1—Cl1 | 2.2115 (17) |
C12—H12 | 0.9300 | Zn1—N2 | 2.057 (4) |
C13—C14 | 1.389 (7) | Zn1—O1i | 1.932 (4) |
C13—H13 | 0.9300 | Zn1—N1ii | 2.057 (4) |
C14—C15 | 1.389 (6) | ||
O2—C1—O1 | 126.5 (6) | C17—C16—C14 | 122.1 (5) |
O2—C1—C2 | 117.7 (6) | C20—C16—C14 | 122.2 (5) |
O1—C1—C2 | 115.7 (6) | C16—C17—C18 | 120.6 (6) |
C7—C2—C3 | 118.3 (5) | C16—C17—H17 | 119.7 |
C7—C2—C1 | 121.2 (5) | C18—C17—H17 | 119.7 |
C3—C2—C1 | 120.4 (6) | N1—C18—C17 | 123.2 (6) |
C2—C3—C4 | 120.4 (6) | N1—C18—H18 | 118.4 |
C2—C3—H3 | 119.8 | C17—C18—H18 | 118.4 |
C4—C3—H3 | 119.8 | N1—C19—C20 | 122.9 (5) |
C5—C4—C3 | 121.2 (6) | N1—C19—H19 | 118.6 |
C5—C4—H4 | 119.4 | C20—C19—H19 | 118.6 |
C3—C4—H4 | 119.4 | C16—C20—C19 | 120.9 (5) |
C4—C5—C6 | 118.2 (5) | C16—C20—H20 | 119.6 |
C4—C5—C8 | 123.1 (5) | C19—C20—H20 | 119.6 |
C6—C5—C8 | 118.6 (5) | C26—C21—N3 | 131.1 (5) |
C7—C6—C5 | 120.5 (5) | C26—C21—C22 | 123.3 (5) |
C7—C6—H6 | 119.7 | N3—C21—C22 | 105.6 (4) |
C5—C6—H6 | 119.7 | C23—C22—C21 | 119.9 (5) |
C2—C7—C6 | 121.3 (5) | C23—C22—N2 | 130.2 (5) |
C2—C7—H7 | 119.4 | C21—C22—N2 | 109.9 (4) |
C6—C7—H7 | 119.4 | C24—C23—C22 | 117.6 (5) |
N3—C8—C5 | 113.4 (4) | C24—C23—H23 | 121.2 |
N3—C8—H8A | 108.9 | C22—C23—H23 | 121.2 |
C5—C8—H8A | 108.9 | C23—C24—C25 | 122.0 (5) |
N3—C8—H8B | 108.9 | C23—C24—H24 | 119.0 |
C5—C8—H8B | 108.9 | C25—C24—H24 | 119.0 |
H8A—C8—H8B | 107.7 | C24—C25—C26 | 121.5 (5) |
N2—C9—N3 | 112.0 (5) | C24—C25—H25 | 119.3 |
N2—C9—C10 | 124.0 (5) | C26—C25—H25 | 119.3 |
N3—C9—C10 | 123.8 (5) | C21—C26—C25 | 115.7 (5) |
C11—C10—C15 | 119.1 (5) | C21—C26—H26 | 122.2 |
C11—C10—C9 | 117.8 (5) | C25—C26—H26 | 122.2 |
C15—C10—C9 | 123.2 (5) | C19—N1—C18 | 116.7 (5) |
C10—C11—C12 | 120.2 (5) | C19—N1—Zn1ii | 123.4 (4) |
C10—C11—H11 | 119.9 | C18—N1—Zn1ii | 119.0 (4) |
C12—C11—H11 | 119.9 | C9—N2—C22 | 105.2 (4) |
C13—C12—C11 | 120.1 (6) | C9—N2—Zn1 | 122.9 (4) |
C13—C12—H12 | 120.0 | C22—N2—Zn1 | 128.0 (4) |
C11—C12—H12 | 120.0 | C9—N3—C21 | 107.3 (4) |
C12—C13—C14 | 120.9 (6) | C9—N3—C8 | 127.2 (4) |
C12—C13—H13 | 119.5 | C21—N3—C8 | 125.5 (5) |
C14—C13—H13 | 119.5 | C1—O1—Zn1iii | 119.9 (4) |
C13—C14—C15 | 117.6 (5) | O1i—Zn1—N1ii | 117.60 (18) |
C13—C14—C16 | 121.1 (5) | O1i—Zn1—N2 | 109.39 (17) |
C15—C14—C16 | 121.3 (5) | N1ii—Zn1—N2 | 98.60 (17) |
C10—C15—C14 | 122.0 (5) | O1i—Zn1—Cl1 | 106.89 (13) |
C10—C15—H15 | 119.0 | N1ii—Zn1—Cl1 | 109.25 (15) |
C14—C15—H15 | 119.0 | N2—Zn1—Cl1 | 115.34 (13) |
C17—C16—C20 | 115.7 (5) | ||
O2—C1—C2—C7 | 14.3 (8) | N3—C21—C22—C23 | −177.2 (5) |
O1—C1—C2—C7 | −166.9 (5) | C26—C21—C22—N2 | 177.3 (5) |
O2—C1—C2—C3 | −164.6 (5) | N3—C21—C22—N2 | −0.3 (6) |
O1—C1—C2—C3 | 14.2 (8) | C21—C22—C23—C24 | 1.8 (8) |
C7—C2—C3—C4 | 0.1 (8) | N2—C22—C23—C24 | −174.3 (5) |
C1—C2—C3—C4 | 179.0 (5) | C22—C23—C24—C25 | −2.5 (8) |
C2—C3—C4—C5 | 1.3 (9) | C23—C24—C25—C26 | 1.0 (9) |
C3—C4—C5—C6 | −1.6 (8) | N3—C21—C26—C25 | 175.0 (5) |
C3—C4—C5—C8 | 178.1 (5) | C22—C21—C26—C25 | −2.0 (8) |
C4—C5—C6—C7 | 0.7 (8) | C24—C25—C26—C21 | 1.3 (8) |
C8—C5—C6—C7 | −179.1 (5) | C20—C19—N1—C18 | −0.5 (9) |
C3—C2—C7—C6 | −1.0 (8) | C20—C19—N1—Zn1ii | −169.5 (4) |
C1—C2—C7—C6 | −179.9 (5) | C17—C18—N1—C19 | −0.5 (9) |
C5—C6—C7—C2 | 0.6 (8) | C17—C18—N1—Zn1ii | 169.0 (4) |
C4—C5—C8—N3 | −20.9 (8) | N3—C9—N2—C22 | 3.2 (6) |
C6—C5—C8—N3 | 158.9 (5) | C10—C9—N2—C22 | −172.1 (5) |
N2—C9—C10—C11 | 50.8 (8) | N3—C9—N2—Zn1 | −156.2 (3) |
N3—C9—C10—C11 | −123.9 (6) | C10—C9—N2—Zn1 | 28.5 (7) |
N2—C9—C10—C15 | −130.3 (6) | C23—C22—N2—C9 | 174.7 (5) |
N3—C9—C10—C15 | 55.0 (8) | C21—C22—N2—C9 | −1.7 (6) |
C15—C10—C11—C12 | 0.9 (9) | C23—C22—N2—Zn1 | −27.3 (8) |
C9—C10—C11—C12 | 179.9 (5) | C21—C22—N2—Zn1 | 156.3 (3) |
C10—C11—C12—C13 | −0.8 (10) | N2—C9—N3—C21 | −3.5 (6) |
C11—C12—C13—C14 | 0.8 (10) | C10—C9—N3—C21 | 171.8 (5) |
C12—C13—C14—C15 | −0.8 (9) | N2—C9—N3—C8 | 177.8 (5) |
C12—C13—C14—C16 | 177.9 (5) | C10—C9—N3—C8 | −6.9 (8) |
C11—C10—C15—C14 | −1.0 (8) | C26—C21—N3—C9 | −175.2 (6) |
C9—C10—C15—C14 | −179.9 (5) | C22—C21—N3—C9 | 2.2 (5) |
C13—C14—C15—C10 | 0.9 (8) | C26—C21—N3—C8 | 3.6 (9) |
C16—C14—C15—C10 | −177.8 (5) | C22—C21—N3—C8 | −179.1 (4) |
C13—C14—C16—C17 | −10.2 (9) | C5—C8—N3—C9 | −84.4 (6) |
C15—C14—C16—C17 | 168.5 (5) | C5—C8—N3—C21 | 97.1 (6) |
C13—C14—C16—C20 | 171.6 (6) | O2—C1—O1—Zn1iii | −6.2 (9) |
C15—C14—C16—C20 | −9.7 (9) | C2—C1—O1—Zn1iii | 175.2 (3) |
C20—C16—C17—C18 | −1.3 (9) | C9—N2—Zn1—O1i | 157.4 (4) |
C14—C16—C17—C18 | −179.6 (5) | C22—N2—Zn1—O1i | 3.0 (4) |
C16—C17—C18—N1 | 1.5 (10) | C9—N2—Zn1—N1ii | 34.1 (5) |
C17—C16—C20—C19 | 0.3 (9) | C22—N2—Zn1—N1ii | −120.4 (4) |
C14—C16—C20—C19 | 178.6 (5) | C9—N2—Zn1—Cl1 | −82.1 (4) |
N1—C19—C20—C16 | 0.6 (9) | C22—N2—Zn1—Cl1 | 123.5 (4) |
C26—C21—C22—C23 | 0.5 (8) |
Symmetry codes: (i) x−1/2, −y+5/2, z−1/2; (ii) −x+1, −y+2, −z+1; (iii) x+1/2, −y+5/2, z+1/2. |
[Zn(C26H18N3O2)Br] | F(000) = 1104 |
Mr = 549.71 | Dx = 1.621 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 1509 reflections |
a = 13.046 (4) Å | θ = 2.6–18.9° |
b = 10.276 (3) Å | µ = 2.89 mm−1 |
c = 17.437 (5) Å | T = 298 K |
β = 105.568 (5)° | Bar, yellow |
V = 2252.0 (12) Å3 | 0.11 × 0.09 × 0.07 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 4005 independent reflections |
Radiation source: fine-focus sealed tube | 2162 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
φ and ω scans | θmax = 25.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −15→14 |
Tmin = 0.741, Tmax = 0.823 | k = −12→11 |
11194 measured reflections | l = −18→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 0.82 | w = 1/[σ2(Fo2) + (0.0265P)2] where P = (Fo2 + 2Fc2)/3 |
4005 reflections | (Δ/σ)max = 0.001 |
298 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9109 (4) | 1.2264 (6) | 0.6107 (3) | 0.0424 (13) | |
C2 | 0.8788 (3) | 1.1320 (5) | 0.5416 (3) | 0.0371 (12) | |
C3 | 0.8303 (4) | 1.1750 (5) | 0.4656 (3) | 0.0444 (13) | |
H3 | 0.8162 | 1.2632 | 0.4563 | 0.053* | |
C4 | 0.8023 (4) | 1.0873 (5) | 0.4025 (3) | 0.0478 (14) | |
H4 | 0.7706 | 1.1180 | 0.3515 | 0.057* | |
C5 | 0.8205 (3) | 0.9566 (5) | 0.4142 (3) | 0.0343 (11) | |
C6 | 0.8688 (3) | 0.9139 (5) | 0.4902 (3) | 0.0421 (13) | |
H6 | 0.8825 | 0.8257 | 0.4996 | 0.050* | |
C7 | 0.8971 (3) | 1.0020 (5) | 0.5527 (3) | 0.0452 (14) | |
H7 | 0.9296 | 0.9713 | 0.6036 | 0.054* | |
C8 | 0.7889 (3) | 0.8580 (4) | 0.3466 (2) | 0.0394 (12) | |
H8A | 0.8515 | 0.8356 | 0.3294 | 0.047* | |
H8B | 0.7642 | 0.7793 | 0.3667 | 0.047* | |
C9 | 0.6006 (4) | 0.9025 (4) | 0.2694 (3) | 0.0356 (12) | |
C10 | 0.5488 (4) | 0.8353 (5) | 0.3240 (3) | 0.0368 (12) | |
C11 | 0.4732 (4) | 0.7424 (5) | 0.2930 (3) | 0.0533 (15) | |
H11 | 0.4560 | 0.7238 | 0.2388 | 0.064* | |
C12 | 0.4229 (4) | 0.6768 (5) | 0.3411 (3) | 0.0639 (17) | |
H12 | 0.3725 | 0.6133 | 0.3196 | 0.077* | |
C13 | 0.4470 (4) | 0.7052 (5) | 0.4216 (3) | 0.0558 (15) | |
H13 | 0.4128 | 0.6603 | 0.4539 | 0.067* | |
C14 | 0.5218 (4) | 0.8000 (5) | 0.4547 (3) | 0.0387 (12) | |
C15 | 0.5724 (3) | 0.8635 (4) | 0.4048 (3) | 0.0345 (12) | |
H15 | 0.6232 | 0.9266 | 0.4259 | 0.041* | |
C16 | 0.5460 (4) | 0.8339 (5) | 0.5405 (3) | 0.0361 (12) | |
C17 | 0.4840 (4) | 0.7881 (5) | 0.5886 (3) | 0.0480 (14) | |
H17 | 0.4258 | 0.7349 | 0.5671 | 0.058* | |
C18 | 0.5091 (4) | 0.8216 (5) | 0.6680 (3) | 0.0517 (14) | |
H18 | 0.4672 | 0.7876 | 0.6987 | 0.062* | |
C19 | 0.6483 (4) | 0.9450 (5) | 0.6579 (3) | 0.0461 (13) | |
H19 | 0.7047 | 1.0002 | 0.6808 | 0.055* | |
C20 | 0.6296 (4) | 0.9141 (5) | 0.5777 (3) | 0.0447 (13) | |
H20 | 0.6739 | 0.9477 | 0.5488 | 0.054* | |
C21 | 0.7248 (4) | 0.9568 (5) | 0.2095 (3) | 0.0368 (12) | |
C22 | 0.6233 (4) | 0.9894 (4) | 0.1623 (3) | 0.0379 (13) | |
C23 | 0.6128 (4) | 1.0407 (5) | 0.0860 (3) | 0.0458 (13) | |
H23 | 0.5467 | 1.0656 | 0.0537 | 0.055* | |
C24 | 0.7025 (5) | 1.0528 (5) | 0.0605 (3) | 0.0513 (14) | |
H24 | 0.6967 | 1.0827 | 0.0091 | 0.062* | |
C25 | 0.8021 (5) | 1.0217 (5) | 0.1093 (3) | 0.0550 (15) | |
H25 | 0.8615 | 1.0335 | 0.0902 | 0.066* | |
C26 | 0.8161 (4) | 0.9736 (5) | 0.1856 (3) | 0.0477 (13) | |
H26 | 0.8831 | 0.9539 | 0.2185 | 0.057* | |
Br1 | 0.25500 (4) | 0.88562 (6) | 0.14695 (3) | 0.0644 (2) | |
N1 | 0.5893 (3) | 0.8994 (4) | 0.7036 (2) | 0.0408 (10) | |
N2 | 0.5465 (3) | 0.9561 (4) | 0.2007 (2) | 0.0378 (10) | |
N3 | 0.7066 (3) | 0.9034 (4) | 0.2782 (2) | 0.0355 (10) | |
O1 | 0.8729 (3) | 1.3376 (3) | 0.59808 (18) | 0.0586 (10) | |
O2 | 0.9719 (3) | 1.1888 (4) | 0.6723 (2) | 0.0682 (12) | |
Zn1 | 0.39633 (4) | 1.03479 (6) | 0.18244 (3) | 0.04375 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.034 (3) | 0.057 (4) | 0.037 (3) | −0.003 (3) | 0.011 (3) | −0.012 (3) |
C2 | 0.031 (3) | 0.038 (4) | 0.042 (3) | 0.004 (2) | 0.010 (2) | −0.003 (2) |
C3 | 0.049 (3) | 0.037 (3) | 0.045 (3) | 0.004 (3) | 0.009 (3) | −0.002 (3) |
C4 | 0.055 (3) | 0.047 (4) | 0.035 (3) | 0.009 (3) | 0.001 (3) | 0.003 (3) |
C5 | 0.028 (3) | 0.038 (3) | 0.034 (3) | 0.003 (3) | 0.005 (2) | −0.003 (2) |
C6 | 0.045 (3) | 0.037 (4) | 0.042 (3) | 0.011 (3) | 0.008 (3) | 0.004 (3) |
C7 | 0.038 (3) | 0.059 (4) | 0.033 (3) | 0.002 (3) | −0.001 (2) | 0.000 (3) |
C8 | 0.039 (3) | 0.039 (3) | 0.038 (3) | 0.004 (2) | 0.007 (2) | 0.000 (2) |
C9 | 0.044 (3) | 0.034 (3) | 0.027 (3) | −0.002 (3) | 0.007 (2) | −0.001 (2) |
C10 | 0.039 (3) | 0.037 (3) | 0.031 (3) | 0.006 (2) | 0.004 (2) | 0.007 (2) |
C11 | 0.062 (4) | 0.060 (4) | 0.035 (3) | −0.013 (3) | 0.008 (3) | 0.002 (3) |
C12 | 0.077 (4) | 0.065 (4) | 0.045 (4) | −0.031 (3) | 0.009 (3) | −0.003 (3) |
C13 | 0.066 (4) | 0.060 (4) | 0.044 (4) | −0.015 (3) | 0.019 (3) | 0.006 (3) |
C14 | 0.039 (3) | 0.039 (4) | 0.038 (3) | 0.004 (3) | 0.010 (3) | 0.003 (2) |
C15 | 0.031 (3) | 0.033 (3) | 0.037 (3) | 0.001 (2) | 0.005 (2) | −0.002 (2) |
C16 | 0.037 (3) | 0.041 (3) | 0.032 (3) | 0.006 (2) | 0.014 (2) | 0.009 (2) |
C17 | 0.051 (3) | 0.054 (4) | 0.040 (3) | −0.007 (3) | 0.012 (3) | −0.002 (3) |
C18 | 0.060 (4) | 0.063 (4) | 0.039 (3) | −0.005 (3) | 0.024 (3) | 0.007 (3) |
C19 | 0.040 (3) | 0.053 (4) | 0.045 (3) | −0.001 (3) | 0.011 (3) | 0.004 (3) |
C20 | 0.046 (3) | 0.055 (4) | 0.036 (3) | −0.004 (3) | 0.018 (3) | 0.001 (2) |
C21 | 0.044 (3) | 0.034 (3) | 0.031 (3) | 0.000 (3) | 0.005 (2) | −0.010 (2) |
C22 | 0.051 (3) | 0.036 (4) | 0.028 (3) | −0.009 (2) | 0.013 (3) | −0.004 (2) |
C23 | 0.062 (4) | 0.035 (3) | 0.037 (3) | −0.008 (3) | 0.007 (3) | −0.006 (2) |
C24 | 0.076 (4) | 0.043 (4) | 0.038 (3) | −0.011 (3) | 0.022 (3) | −0.007 (3) |
C25 | 0.071 (4) | 0.044 (4) | 0.064 (4) | −0.011 (3) | 0.043 (3) | −0.010 (3) |
C26 | 0.047 (3) | 0.044 (4) | 0.059 (4) | −0.004 (3) | 0.025 (3) | −0.006 (3) |
Br1 | 0.0577 (4) | 0.0680 (5) | 0.0661 (4) | −0.0171 (3) | 0.0141 (3) | −0.0023 (3) |
N1 | 0.043 (3) | 0.041 (3) | 0.039 (3) | −0.002 (2) | 0.013 (2) | 0.002 (2) |
N2 | 0.035 (2) | 0.044 (3) | 0.033 (2) | −0.003 (2) | 0.0057 (19) | 0.005 (2) |
N3 | 0.034 (2) | 0.042 (3) | 0.027 (2) | 0.006 (2) | 0.0041 (19) | −0.0030 (18) |
O1 | 0.080 (3) | 0.045 (3) | 0.047 (2) | 0.001 (2) | 0.0105 (19) | −0.0118 (18) |
O2 | 0.068 (3) | 0.081 (3) | 0.045 (2) | 0.017 (2) | −0.005 (2) | −0.018 (2) |
Zn1 | 0.0465 (4) | 0.0475 (4) | 0.0364 (4) | −0.0007 (3) | 0.0094 (3) | 0.0049 (3) |
C1—O2 | 1.216 (5) | C14—C16 | 1.485 (6) |
C1—O1 | 1.241 (6) | C15—H15 | 0.9300 |
C1—C2 | 1.515 (6) | C16—C20 | 1.382 (6) |
C2—C7 | 1.362 (6) | C16—C17 | 1.394 (5) |
C2—C3 | 1.380 (6) | C17—C18 | 1.379 (6) |
C3—C4 | 1.392 (6) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—N1 | 1.331 (5) |
C4—C5 | 1.369 (6) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—N1 | 1.333 (5) |
C5—C6 | 1.377 (5) | C19—C20 | 1.390 (6) |
C5—C8 | 1.525 (6) | C19—H19 | 0.9300 |
C6—C7 | 1.389 (6) | C20—H20 | 0.9300 |
C6—H6 | 0.9300 | C21—C26 | 1.375 (6) |
C7—H7 | 0.9300 | C21—N3 | 1.394 (5) |
C8—N3 | 1.452 (5) | C21—C22 | 1.400 (6) |
C8—H8A | 0.9700 | C22—N2 | 1.390 (5) |
C8—H8B | 0.9700 | C22—C23 | 1.403 (6) |
C9—N2 | 1.334 (5) | C23—C24 | 1.365 (6) |
C9—N3 | 1.349 (5) | C23—H23 | 0.9300 |
C9—C10 | 1.478 (6) | C24—C25 | 1.387 (6) |
C10—C11 | 1.374 (6) | C24—H24 | 0.9300 |
C10—C15 | 1.390 (5) | C25—C26 | 1.384 (6) |
C11—C12 | 1.373 (6) | C25—H25 | 0.9300 |
C11—H11 | 0.9300 | C26—H26 | 0.9300 |
C12—C13 | 1.384 (6) | Zn1—Br1 | 2.3495 (9) |
C12—H12 | 0.9300 | Zn1—N2 | 2.064 (4) |
C13—C14 | 1.390 (6) | Zn1—O1i | 1.933 (3) |
C13—H13 | 0.9300 | Zn1—N1ii | 2.059 (4) |
C14—C15 | 1.388 (5) | ||
O2—C1—O1 | 125.8 (5) | C20—C16—C14 | 122.7 (4) |
O2—C1—C2 | 118.3 (5) | C17—C16—C14 | 121.8 (4) |
O1—C1—C2 | 115.9 (5) | C18—C17—C16 | 120.1 (5) |
C7—C2—C3 | 117.9 (4) | C18—C17—H17 | 120.0 |
C7—C2—C1 | 121.0 (5) | C16—C17—H17 | 120.0 |
C3—C2—C1 | 121.1 (5) | N1—C18—C17 | 124.3 (4) |
C2—C3—C4 | 120.5 (5) | N1—C18—H18 | 117.9 |
C2—C3—H3 | 119.8 | C17—C18—H18 | 117.9 |
C4—C3—H3 | 119.8 | N1—C19—C20 | 123.2 (5) |
C5—C4—C3 | 121.3 (5) | N1—C19—H19 | 118.4 |
C5—C4—H4 | 119.4 | C20—C19—H19 | 118.4 |
C3—C4—H4 | 119.4 | C16—C20—C19 | 120.8 (4) |
C4—C5—C6 | 118.2 (4) | C16—C20—H20 | 119.6 |
C4—C5—C8 | 122.5 (4) | C19—C20—H20 | 119.6 |
C6—C5—C8 | 119.4 (4) | C26—C21—N3 | 132.2 (4) |
C5—C6—C7 | 120.3 (5) | C26—C21—C22 | 123.4 (4) |
C5—C6—H6 | 119.9 | N3—C21—C22 | 104.3 (4) |
C7—C6—H6 | 119.9 | N2—C22—C21 | 110.3 (4) |
C2—C7—C6 | 121.9 (4) | N2—C22—C23 | 130.6 (5) |
C2—C7—H7 | 119.1 | C21—C22—C23 | 119.0 (4) |
C6—C7—H7 | 119.1 | C24—C23—C22 | 118.0 (5) |
N3—C8—C5 | 114.1 (4) | C24—C23—H23 | 121.0 |
N3—C8—H8A | 108.7 | C22—C23—H23 | 121.0 |
C5—C8—H8A | 108.7 | C23—C24—C25 | 121.6 (5) |
N3—C8—H8B | 108.7 | C23—C24—H24 | 119.2 |
C5—C8—H8B | 108.7 | C25—C24—H24 | 119.2 |
H8A—C8—H8B | 107.6 | C26—C25—C24 | 122.1 (5) |
N2—C9—N3 | 112.3 (4) | C26—C25—H25 | 118.9 |
N2—C9—C10 | 123.1 (4) | C24—C25—H25 | 118.9 |
N3—C9—C10 | 124.2 (4) | C21—C26—C25 | 115.8 (5) |
C11—C10—C15 | 118.9 (4) | C21—C26—H26 | 122.1 |
C11—C10—C9 | 118.4 (4) | C25—C26—H26 | 122.1 |
C15—C10—C9 | 122.7 (4) | C18—N1—C19 | 116.1 (4) |
C12—C11—C10 | 120.8 (5) | C18—N1—Zn1ii | 120.3 (3) |
C12—C11—H11 | 119.6 | C19—N1—Zn1ii | 122.9 (3) |
C10—C11—H11 | 119.6 | C9—N2—C22 | 104.9 (4) |
C11—C12—C13 | 120.0 (5) | C9—N2—Zn1 | 123.5 (3) |
C11—C12—H12 | 120.0 | C22—N2—Zn1 | 127.3 (3) |
C13—C12—H12 | 120.0 | C9—N3—C21 | 108.1 (4) |
C12—C13—C14 | 120.8 (5) | C9—N3—C8 | 126.9 (4) |
C12—C13—H13 | 119.6 | C21—N3—C8 | 125.0 (4) |
C14—C13—H13 | 119.6 | C1—O1—Zn1iii | 121.0 (3) |
C15—C14—C13 | 117.9 (4) | O1i—Zn1—N1ii | 117.81 (16) |
C15—C14—C16 | 120.9 (4) | O1i—Zn1—N2 | 109.49 (15) |
C13—C14—C16 | 121.2 (4) | N1ii—Zn1—N2 | 98.19 (14) |
C14—C15—C10 | 121.7 (4) | O1i—Zn1—Br1 | 106.82 (11) |
C14—C15—H15 | 119.2 | N1ii—Zn1—Br1 | 109.29 (11) |
C10—C15—H15 | 119.2 | N2—Zn1—Br1 | 115.49 (11) |
C20—C16—C17 | 115.5 (4) | ||
O2—C1—C2—C7 | 14.8 (7) | N3—C21—C22—N2 | −0.4 (5) |
O1—C1—C2—C7 | −166.5 (4) | C26—C21—C22—C23 | 0.7 (7) |
O2—C1—C2—C3 | −165.1 (4) | N3—C21—C22—C23 | −177.0 (4) |
O1—C1—C2—C3 | 13.6 (6) | N2—C22—C23—C24 | −173.9 (5) |
C7—C2—C3—C4 | −0.6 (7) | C21—C22—C23—C24 | 1.9 (7) |
C1—C2—C3—C4 | 179.3 (4) | C22—C23—C24—C25 | −3.1 (7) |
C2—C3—C4—C5 | 1.0 (7) | C23—C24—C25—C26 | 1.7 (8) |
C3—C4—C5—C6 | −0.9 (7) | N3—C21—C26—C25 | 174.9 (5) |
C3—C4—C5—C8 | 178.9 (4) | C22—C21—C26—C25 | −2.1 (7) |
C4—C5—C6—C7 | 0.5 (7) | C24—C25—C26—C21 | 0.9 (7) |
C8—C5—C6—C7 | −179.3 (4) | C17—C18—N1—C19 | −0.8 (7) |
C3—C2—C7—C6 | 0.2 (7) | C17—C18—N1—Zn1ii | 170.2 (4) |
C1—C2—C7—C6 | −179.7 (4) | C20—C19—N1—C18 | −0.5 (7) |
C5—C6—C7—C2 | −0.1 (7) | C20—C19—N1—Zn1ii | −171.2 (3) |
C4—C5—C8—N3 | −21.4 (6) | N3—C9—N2—C22 | 2.0 (5) |
C6—C5—C8—N3 | 158.4 (4) | C10—C9—N2—C22 | −170.7 (4) |
N2—C9—C10—C11 | 49.6 (7) | N3—C9—N2—Zn1 | −156.4 (3) |
N3—C9—C10—C11 | −122.2 (5) | C10—C9—N2—Zn1 | 30.9 (6) |
N2—C9—C10—C15 | −129.4 (5) | C21—C22—N2—C9 | −0.9 (5) |
N3—C9—C10—C15 | 58.8 (6) | C23—C22—N2—C9 | 175.1 (5) |
C15—C10—C11—C12 | −1.1 (8) | C21—C22—N2—Zn1 | 156.3 (3) |
C9—C10—C11—C12 | 179.8 (5) | C23—C22—N2—Zn1 | −27.6 (7) |
C10—C11—C12—C13 | 0.9 (8) | N2—C9—N3—C21 | −2.3 (5) |
C11—C12—C13—C14 | 0.2 (8) | C10—C9—N3—C21 | 170.3 (4) |
C12—C13—C14—C15 | −1.0 (7) | N2—C9—N3—C8 | 177.4 (4) |
C12—C13—C14—C16 | 178.2 (4) | C10—C9—N3—C8 | −10.0 (7) |
C13—C14—C15—C10 | 0.7 (7) | C26—C21—N3—C9 | −175.8 (5) |
C16—C14—C15—C10 | −178.4 (4) | C22—C21—N3—C9 | 1.6 (5) |
C11—C10—C15—C14 | 0.3 (7) | C26—C21—N3—C8 | 4.5 (8) |
C9—C10—C15—C14 | 179.3 (4) | C22—C21—N3—C8 | −178.2 (4) |
C15—C14—C16—C20 | −10.1 (7) | C5—C8—N3—C9 | −82.4 (5) |
C13—C14—C16—C20 | 170.8 (5) | C5—C8—N3—C21 | 97.3 (5) |
C15—C14—C16—C17 | 168.9 (4) | O2—C1—O1—Zn1iii | −6.5 (7) |
C13—C14—C16—C17 | −10.2 (7) | C2—C1—O1—Zn1iii | 174.8 (3) |
C20—C16—C17—C18 | −1.0 (7) | C9—N2—Zn1—O1i | 155.6 (3) |
C14—C16—C17—C18 | 179.9 (4) | C22—N2—Zn1—O1i | 2.2 (4) |
C16—C17—C18—N1 | 1.6 (8) | C9—N2—Zn1—N1ii | 32.2 (4) |
C17—C16—C20—C19 | −0.1 (7) | C22—N2—Zn1—N1ii | −121.2 (4) |
C14—C16—C20—C19 | 178.9 (4) | C9—N2—Zn1—Br1 | −83.8 (4) |
N1—C19—C20—C16 | 0.9 (7) | C22—N2—Zn1—Br1 | 122.8 (3) |
C26—C21—C22—N2 | 177.3 (4) |
Symmetry codes: (i) x−1/2, −y+5/2, z−1/2; (ii) −x+1, −y+2, −z+1; (iii) x+1/2, −y+5/2, z+1/2. |
[Zn(C26H18N3O2)I] | F(000) = 1176 |
Mr = 596.70 | Dx = 1.708 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 1762 reflections |
a = 13.212 (8) Å | θ = 2.3–20.1° |
b = 10.480 (6) Å | µ = 2.42 mm−1 |
c = 17.535 (10) Å | T = 298 K |
β = 107.148 (9)° | Block, yellow |
V = 2320 (2) Å3 | 0.18 × 0.15 × 0.10 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 4134 independent reflections |
Radiation source: fine-focus sealed tube | 2478 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
φ and ω scans | θmax = 25.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→15 |
Tmin = 0.670, Tmax = 0.794 | k = −12→12 |
11584 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0471P)2] where P = (Fo2 + 2Fc2)/3 |
4134 reflections | (Δ/σ)max = 0.001 |
298 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.66 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.9146 (5) | 1.2248 (7) | 0.6137 (4) | 0.0424 (16) | |
C2 | 0.8823 (4) | 1.1333 (6) | 0.5454 (4) | 0.0377 (15) | |
C3 | 0.8330 (5) | 1.1741 (6) | 0.4688 (4) | 0.0486 (17) | |
H3 | 0.8192 | 1.2606 | 0.4591 | 0.058* | |
C4 | 0.8037 (5) | 1.0890 (6) | 0.4061 (4) | 0.0476 (17) | |
H4 | 0.7711 | 1.1189 | 0.3548 | 0.057* | |
C5 | 0.8225 (4) | 0.9592 (6) | 0.4187 (4) | 0.0374 (15) | |
C6 | 0.8699 (5) | 0.9197 (6) | 0.4948 (4) | 0.0472 (17) | |
H6 | 0.8824 | 0.8331 | 0.5048 | 0.057* | |
C7 | 0.9000 (5) | 1.0048 (7) | 0.5576 (4) | 0.0484 (17) | |
H7 | 0.9326 | 0.9746 | 0.6089 | 0.058* | |
C8 | 0.7906 (5) | 0.8629 (6) | 0.3515 (4) | 0.0437 (16) | |
H8A | 0.8525 | 0.8409 | 0.3354 | 0.052* | |
H8B | 0.7664 | 0.7859 | 0.3714 | 0.052* | |
C9 | 0.6021 (5) | 0.9077 (5) | 0.2717 (3) | 0.0364 (15) | |
C10 | 0.5529 (5) | 0.8417 (6) | 0.3257 (4) | 0.0389 (15) | |
C11 | 0.4791 (6) | 0.7485 (6) | 0.2923 (4) | 0.0563 (19) | |
H11 | 0.4631 | 0.7301 | 0.2382 | 0.068* | |
C12 | 0.4290 (6) | 0.6828 (7) | 0.3391 (4) | 0.069 (2) | |
H12 | 0.3803 | 0.6191 | 0.3166 | 0.083* | |
C13 | 0.4507 (6) | 0.7109 (7) | 0.4190 (4) | 0.060 (2) | |
H13 | 0.4165 | 0.6660 | 0.4500 | 0.072* | |
C14 | 0.5230 (5) | 0.8056 (6) | 0.4539 (4) | 0.0437 (16) | |
C15 | 0.5737 (5) | 0.8687 (6) | 0.4049 (4) | 0.0403 (15) | |
H15 | 0.6235 | 0.9313 | 0.4273 | 0.048* | |
C16 | 0.5442 (5) | 0.8386 (6) | 0.5389 (4) | 0.0388 (15) | |
C17 | 0.4819 (5) | 0.7935 (6) | 0.5849 (4) | 0.0469 (17) | |
H17 | 0.4238 | 0.7417 | 0.5615 | 0.056* | |
C18 | 0.5049 (5) | 0.8241 (6) | 0.6634 (4) | 0.0497 (17) | |
H18 | 0.4625 | 0.7900 | 0.6923 | 0.060* | |
C19 | 0.6451 (5) | 0.9460 (6) | 0.6588 (4) | 0.0451 (16) | |
H19 | 0.7018 | 0.9988 | 0.6836 | 0.054* | |
C20 | 0.6263 (5) | 0.9175 (6) | 0.5789 (4) | 0.0454 (17) | |
H20 | 0.6700 | 0.9524 | 0.5514 | 0.055* | |
C21 | 0.7224 (5) | 0.9599 (5) | 0.2126 (3) | 0.0403 (15) | |
C22 | 0.6221 (5) | 0.9929 (5) | 0.1648 (3) | 0.0368 (15) | |
C23 | 0.6099 (6) | 1.0420 (6) | 0.0893 (4) | 0.0482 (17) | |
H23 | 0.5437 | 1.0655 | 0.0562 | 0.058* | |
C24 | 0.6998 (7) | 1.0549 (6) | 0.0653 (4) | 0.058 (2) | |
H24 | 0.6938 | 1.0873 | 0.0147 | 0.070* | |
C25 | 0.7985 (6) | 1.0207 (6) | 0.1144 (5) | 0.059 (2) | |
H25 | 0.8568 | 1.0294 | 0.0953 | 0.071* | |
C26 | 0.8139 (5) | 0.9748 (6) | 0.1899 (4) | 0.0498 (17) | |
H26 | 0.8808 | 0.9550 | 0.2236 | 0.060* | |
I1 | 0.24507 (4) | 0.88718 (5) | 0.14070 (3) | 0.0680 (2) | |
N1 | 0.5850 (4) | 0.9005 (5) | 0.7016 (3) | 0.0395 (12) | |
N2 | 0.5484 (4) | 0.9611 (5) | 0.2044 (3) | 0.0387 (12) | |
N3 | 0.7079 (4) | 0.9068 (4) | 0.2819 (3) | 0.0375 (12) | |
O1 | 0.8766 (4) | 1.3355 (5) | 0.5999 (3) | 0.0599 (13) | |
O2 | 0.9758 (4) | 1.1918 (5) | 0.6761 (3) | 0.0697 (15) | |
Zn1 | 0.39983 (6) | 1.03942 (7) | 0.18391 (4) | 0.0431 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.038 (4) | 0.059 (5) | 0.031 (4) | −0.001 (3) | 0.012 (3) | −0.008 (4) |
C2 | 0.033 (3) | 0.045 (4) | 0.036 (4) | 0.005 (3) | 0.010 (3) | −0.004 (3) |
C3 | 0.055 (4) | 0.034 (4) | 0.055 (5) | 0.003 (3) | 0.013 (4) | −0.005 (3) |
C4 | 0.056 (4) | 0.051 (4) | 0.030 (4) | 0.000 (3) | 0.003 (3) | 0.001 (3) |
C5 | 0.034 (3) | 0.039 (4) | 0.040 (4) | 0.003 (3) | 0.012 (3) | 0.000 (3) |
C6 | 0.048 (4) | 0.042 (4) | 0.046 (4) | 0.008 (3) | 0.005 (3) | 0.000 (3) |
C7 | 0.050 (4) | 0.063 (5) | 0.028 (4) | 0.001 (4) | 0.005 (3) | −0.004 (3) |
C8 | 0.049 (4) | 0.040 (4) | 0.040 (4) | 0.006 (3) | 0.009 (3) | −0.005 (3) |
C9 | 0.042 (4) | 0.035 (4) | 0.032 (4) | −0.001 (3) | 0.010 (3) | −0.001 (3) |
C10 | 0.040 (4) | 0.040 (4) | 0.037 (4) | 0.007 (3) | 0.012 (3) | 0.003 (3) |
C11 | 0.084 (5) | 0.054 (5) | 0.033 (4) | −0.012 (4) | 0.021 (4) | −0.003 (3) |
C12 | 0.086 (6) | 0.066 (5) | 0.055 (5) | −0.033 (4) | 0.019 (5) | −0.004 (4) |
C13 | 0.079 (5) | 0.063 (5) | 0.044 (4) | −0.018 (4) | 0.027 (4) | 0.006 (4) |
C14 | 0.052 (4) | 0.044 (4) | 0.035 (4) | 0.003 (3) | 0.012 (3) | 0.005 (3) |
C15 | 0.038 (4) | 0.041 (4) | 0.043 (4) | 0.007 (3) | 0.013 (3) | 0.006 (3) |
C16 | 0.040 (4) | 0.043 (4) | 0.035 (4) | 0.006 (3) | 0.015 (3) | 0.007 (3) |
C17 | 0.051 (4) | 0.051 (4) | 0.038 (4) | −0.006 (3) | 0.013 (3) | 0.001 (3) |
C18 | 0.063 (5) | 0.055 (5) | 0.040 (4) | 0.002 (4) | 0.028 (4) | 0.009 (3) |
C19 | 0.046 (4) | 0.048 (4) | 0.040 (4) | −0.001 (3) | 0.011 (3) | 0.000 (3) |
C20 | 0.051 (4) | 0.051 (4) | 0.040 (4) | 0.002 (3) | 0.023 (4) | 0.004 (3) |
C21 | 0.059 (4) | 0.032 (4) | 0.036 (4) | −0.004 (3) | 0.023 (4) | −0.011 (3) |
C22 | 0.047 (4) | 0.036 (4) | 0.027 (3) | −0.002 (3) | 0.010 (3) | −0.006 (3) |
C23 | 0.073 (5) | 0.039 (4) | 0.032 (4) | −0.010 (4) | 0.014 (4) | −0.004 (3) |
C24 | 0.100 (6) | 0.049 (5) | 0.039 (4) | −0.015 (4) | 0.041 (5) | −0.004 (3) |
C25 | 0.077 (6) | 0.051 (5) | 0.065 (5) | −0.012 (4) | 0.044 (5) | −0.015 (4) |
C26 | 0.054 (4) | 0.043 (4) | 0.058 (5) | −0.007 (3) | 0.025 (4) | −0.013 (4) |
I1 | 0.0697 (4) | 0.0723 (4) | 0.0640 (4) | −0.0212 (3) | 0.0228 (3) | −0.0076 (3) |
N1 | 0.046 (3) | 0.043 (3) | 0.031 (3) | 0.001 (3) | 0.014 (3) | 0.004 (3) |
N2 | 0.043 (3) | 0.042 (3) | 0.032 (3) | 0.001 (3) | 0.012 (3) | 0.003 (3) |
N3 | 0.046 (3) | 0.036 (3) | 0.029 (3) | 0.002 (2) | 0.009 (3) | −0.005 (2) |
O1 | 0.071 (3) | 0.054 (3) | 0.049 (3) | 0.001 (3) | 0.008 (3) | −0.014 (2) |
O2 | 0.071 (3) | 0.082 (4) | 0.049 (3) | 0.016 (3) | 0.007 (3) | −0.020 (3) |
Zn1 | 0.0488 (5) | 0.0474 (5) | 0.0335 (4) | −0.0006 (4) | 0.0127 (4) | 0.0055 (4) |
C1—O2 | 1.203 (7) | C14—C16 | 1.474 (8) |
C1—O1 | 1.259 (7) | C15—H15 | 0.9300 |
C1—C2 | 1.495 (8) | C16—C20 | 1.380 (8) |
C2—C7 | 1.373 (8) | C16—C17 | 1.394 (7) |
C2—C3 | 1.377 (8) | C17—C18 | 1.357 (8) |
C3—C4 | 1.379 (8) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—N1 | 1.339 (8) |
C4—C5 | 1.388 (8) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—N1 | 1.331 (7) |
C5—C6 | 1.361 (8) | C19—C20 | 1.382 (8) |
C5—C8 | 1.514 (8) | C19—H19 | 0.9300 |
C6—C7 | 1.381 (8) | C20—H20 | 0.9300 |
C6—H6 | 0.9300 | C21—C22 | 1.387 (8) |
C7—H7 | 0.9300 | C21—C26 | 1.389 (8) |
C8—N3 | 1.453 (7) | C21—N3 | 1.399 (7) |
C8—H8A | 0.9700 | C22—C23 | 1.385 (8) |
C8—H8B | 0.9700 | C22—N2 | 1.393 (7) |
C9—N2 | 1.310 (7) | C23—C24 | 1.379 (8) |
C9—N3 | 1.355 (7) | C23—H23 | 0.9300 |
C9—C10 | 1.470 (8) | C24—C25 | 1.381 (9) |
C10—C15 | 1.364 (8) | C24—H24 | 0.9300 |
C10—C11 | 1.382 (8) | C25—C26 | 1.367 (9) |
C11—C12 | 1.381 (8) | C25—H25 | 0.9300 |
C11—H11 | 0.9300 | C26—H26 | 0.9300 |
C12—C13 | 1.376 (9) | Zn1—I1 | 2.5273 (13) |
C12—H12 | 0.9300 | Zn1—N2 | 2.059 (5) |
C13—C14 | 1.388 (9) | Zn1—O1i | 1.928 (4) |
C13—H13 | 0.9300 | Zn1—N1ii | 2.057 (5) |
C14—C15 | 1.401 (8) | ||
O2—C1—O1 | 124.2 (6) | C20—C16—C14 | 122.8 (5) |
O2—C1—C2 | 120.1 (7) | C17—C16—C14 | 122.5 (6) |
O1—C1—C2 | 115.7 (6) | C18—C17—C16 | 120.8 (6) |
C7—C2—C3 | 117.8 (6) | C18—C17—H17 | 119.6 |
C7—C2—C1 | 120.6 (6) | C16—C17—H17 | 119.6 |
C3—C2—C1 | 121.6 (6) | N1—C18—C17 | 123.8 (6) |
C2—C3—C4 | 121.2 (6) | N1—C18—H18 | 118.1 |
C2—C3—H3 | 119.4 | C17—C18—H18 | 118.1 |
C4—C3—H3 | 119.4 | N1—C19—C20 | 122.3 (6) |
C3—C4—C5 | 120.8 (6) | N1—C19—H19 | 118.8 |
C3—C4—H4 | 119.6 | C20—C19—H19 | 118.8 |
C5—C4—H4 | 119.6 | C16—C20—C19 | 121.6 (6) |
C6—C5—C4 | 117.6 (6) | C16—C20—H20 | 119.2 |
C6—C5—C8 | 120.1 (6) | C19—C20—H20 | 119.2 |
C4—C5—C8 | 122.3 (6) | C22—C21—C26 | 123.8 (6) |
C5—C6—C7 | 121.8 (6) | C22—C21—N3 | 105.8 (5) |
C5—C6—H6 | 119.1 | C26—C21—N3 | 130.4 (6) |
C7—C6—H6 | 119.1 | C23—C22—C21 | 119.5 (6) |
C2—C7—C6 | 120.9 (6) | C23—C22—N2 | 131.6 (6) |
C2—C7—H7 | 119.6 | C21—C22—N2 | 108.8 (5) |
C6—C7—H7 | 119.6 | C24—C23—C22 | 117.4 (6) |
N3—C8—C5 | 114.3 (5) | C24—C23—H23 | 121.3 |
N3—C8—H8A | 108.7 | C22—C23—H23 | 121.3 |
C5—C8—H8A | 108.7 | C23—C24—C25 | 121.6 (6) |
N3—C8—H8B | 108.7 | C23—C24—H24 | 119.2 |
C5—C8—H8B | 108.7 | C25—C24—H24 | 119.2 |
H8A—C8—H8B | 107.6 | C26—C25—C24 | 122.6 (7) |
N2—C9—N3 | 112.7 (5) | C26—C25—H25 | 118.7 |
N2—C9—C10 | 123.8 (6) | C24—C25—H25 | 118.7 |
N3—C9—C10 | 123.2 (5) | C25—C26—C21 | 115.1 (7) |
C15—C10—C11 | 118.9 (6) | C25—C26—H26 | 122.4 |
C15—C10—C9 | 124.3 (6) | C21—C26—H26 | 122.4 |
C11—C10—C9 | 116.8 (5) | C19—N1—C18 | 116.6 (5) |
C12—C11—C10 | 120.2 (6) | C19—N1—Zn1ii | 122.5 (4) |
C12—C11—H11 | 119.9 | C18—N1—Zn1ii | 120.5 (4) |
C10—C11—H11 | 119.9 | C9—N2—C22 | 106.2 (5) |
C13—C12—C11 | 120.3 (7) | C9—N2—Zn1 | 124.3 (4) |
C13—C12—H12 | 119.8 | C22—N2—Zn1 | 126.0 (4) |
C11—C12—H12 | 119.8 | C9—N3—C21 | 106.5 (5) |
C12—C13—C14 | 120.8 (6) | C9—N3—C8 | 127.1 (5) |
C12—C13—H13 | 119.6 | C21—N3—C8 | 126.4 (5) |
C14—C13—H13 | 119.6 | C1—O1—Zn1iii | 121.0 (4) |
C13—C14—C15 | 117.3 (6) | O1i—Zn1—N1ii | 119.0 (2) |
C13—C14—C16 | 121.0 (6) | O1i—Zn1—N2 | 109.48 (19) |
C15—C14—C16 | 121.8 (6) | N1ii—Zn1—N2 | 97.95 (19) |
C10—C15—C14 | 122.5 (6) | O1i—Zn1—I1 | 105.52 (15) |
C10—C15—H15 | 118.7 | N1ii—Zn1—I1 | 108.87 (15) |
C14—C15—H15 | 118.7 | N2—Zn1—I1 | 116.48 (14) |
C20—C16—C17 | 114.8 (6) | ||
O2—C1—C2—C7 | 16.1 (9) | N3—C21—C22—C23 | −176.5 (5) |
O1—C1—C2—C7 | −166.2 (6) | C26—C21—C22—N2 | 177.8 (5) |
O2—C1—C2—C3 | −164.7 (6) | N3—C21—C22—N2 | 0.3 (6) |
O1—C1—C2—C3 | 13.0 (8) | C21—C22—C23—C24 | 0.4 (9) |
C7—C2—C3—C4 | −0.9 (9) | N2—C22—C23—C24 | −175.5 (6) |
C1—C2—C3—C4 | 179.8 (5) | C22—C23—C24—C25 | −0.3 (9) |
C2—C3—C4—C5 | 0.5 (9) | C23—C24—C25—C26 | −1.3 (11) |
C3—C4—C5—C6 | 0.4 (9) | C24—C25—C26—C21 | 2.5 (10) |
C3—C4—C5—C8 | 179.4 (5) | C22—C21—C26—C25 | −2.4 (9) |
C4—C5—C6—C7 | −0.8 (9) | N3—C21—C26—C25 | 174.4 (6) |
C8—C5—C6—C7 | −179.9 (6) | C20—C19—N1—C18 | 0.5 (9) |
C3—C2—C7—C6 | 0.5 (9) | C20—C19—N1—Zn1ii | −171.8 (5) |
C1—C2—C7—C6 | 179.7 (5) | C17—C18—N1—C19 | −1.0 (9) |
C5—C6—C7—C2 | 0.4 (10) | C17—C18—N1—Zn1ii | 171.4 (5) |
C6—C5—C8—N3 | 157.7 (5) | N3—C9—N2—C22 | 2.9 (6) |
C4—C5—C8—N3 | −21.4 (8) | C10—C9—N2—C22 | −169.9 (5) |
N2—C9—C10—C15 | −126.6 (7) | N3—C9—N2—Zn1 | −156.9 (4) |
N3—C9—C10—C15 | 61.4 (8) | C10—C9—N2—Zn1 | 30.4 (8) |
N2—C9—C10—C11 | 51.8 (8) | C23—C22—N2—C9 | 174.4 (6) |
N3—C9—C10—C11 | −120.1 (7) | C21—C22—N2—C9 | −1.9 (6) |
C15—C10—C11—C12 | −1.1 (10) | C23—C22—N2—Zn1 | −26.4 (9) |
C9—C10—C11—C12 | −179.7 (6) | C21—C22—N2—Zn1 | 157.4 (4) |
C10—C11—C12—C13 | 1.1 (11) | N2—C9—N3—C21 | −2.7 (6) |
C11—C12—C13—C14 | 0.1 (12) | C10—C9—N3—C21 | 170.1 (5) |
C12—C13—C14—C15 | −1.2 (10) | N2—C9—N3—C8 | 175.7 (5) |
C12—C13—C14—C16 | 178.2 (7) | C10—C9—N3—C8 | −11.5 (9) |
C11—C10—C15—C14 | −0.1 (9) | C22—C21—N3—C9 | 1.4 (6) |
C9—C10—C15—C14 | 178.3 (6) | C26—C21—N3—C9 | −175.9 (6) |
C13—C14—C15—C10 | 1.2 (9) | C22—C21—N3—C8 | −177.1 (5) |
C16—C14—C15—C10 | −178.2 (6) | C26—C21—N3—C8 | 5.6 (9) |
C13—C14—C16—C20 | 169.8 (6) | C5—C8—N3—C9 | −81.2 (7) |
C15—C14—C16—C20 | −10.7 (9) | C5—C8—N3—C21 | 96.9 (6) |
C13—C14—C16—C17 | −10.9 (9) | O2—C1—O1—Zn1iii | −8.0 (9) |
C15—C14—C16—C17 | 168.5 (6) | C2—C1—O1—Zn1iii | 174.4 (4) |
C20—C16—C17—C18 | −1.8 (9) | C9—N2—Zn1—O1i | 156.2 (5) |
C14—C16—C17—C18 | 178.9 (6) | C22—N2—Zn1—O1i | 0.5 (5) |
C16—C17—C18—N1 | 1.8 (10) | C9—N2—Zn1—N1ii | 31.5 (5) |
C17—C16—C20—C19 | 1.4 (9) | C22—N2—Zn1—N1ii | −124.2 (5) |
C14—C16—C20—C19 | −179.4 (6) | C9—N2—Zn1—I1 | −84.2 (5) |
N1—C19—C20—C16 | −0.7 (10) | C22—N2—Zn1—I1 | 120.0 (4) |
C26—C21—C22—C23 | 1.0 (9) |
Symmetry codes: (i) x−1/2, −y+5/2, z−1/2; (ii) −x+1, −y+2, −z+1; (iii) x+1/2, −y+5/2, z+1/2. |